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Novel pyrido sulfur nitrogen 7-membered ring derivatives adopted as anti-tumor drugs, preparation method and applications thereof

An anti-tumor drug, drug technology, applied in the direction of anti-tumor drugs, drug combinations, pharmaceutical formulations, etc., can solve the problem of drug resistance of anti-cancer drugs

Active Publication Date: 2012-12-05
CHANGCHUN DISCOVERY SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

H460 TaxR Cells overexpress P-glycoprotein and are therefore resistant to many known anticancer drugs

Method used

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  • Novel pyrido sulfur nitrogen 7-membered ring derivatives adopted as anti-tumor drugs, preparation method and applications thereof
  • Novel pyrido sulfur nitrogen 7-membered ring derivatives adopted as anti-tumor drugs, preparation method and applications thereof
  • Novel pyrido sulfur nitrogen 7-membered ring derivatives adopted as anti-tumor drugs, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0208] Example 1: Synthesis of Multi-Substituted Pyridothiazapine Seven-membered Ring Derivatives

[0209] Experimental route:

[0210]

[0211] Synthesis of nitrophenylthiopyridine derivative 2:

[0212]

[0213] Add 40mL of absolute ethanol and sodium (0.92g, 40mmol) to a 100mL single-necked flask, and stir magnetically. After the sodium has reacted, cool in an ice-water bath, add thiophenol (40mmol), and after it dissolves, add chlorinated Nitropyridine 1 (40 mmol), reacted for 20 minutes after the addition, filtered with suction, washed with water, and dried to obtain product 2.

[0214] 2-(4-Methoxyphenylthio)-3-nitropyridine 2.1: mp: 140-142°C; 98%; 1 H NMR (CDCl 3 )δ8.52-8.47 (m, 2H), 7.47 (d, J=9.0, 2H), 7.19-7.14 (m, 1H), 6.98 (d, J=9.0, 2H), 3.86 (s, 3H); ES-MS m / z 263.0[M+H + ].

[0215] 2-(3-Methoxyphenylthio)-3-nitropyridine 2.2: mp: 84-85°C; 94%; 1 H NMR (CDCl 3 )δ8.66-8.39 (m, 2H), 7.41 (q, J=7.5, 1H), 7.18 (dd, J=7.6, 7.2, 1H), 7.14-7.00 (m, 1H), ...

Embodiment 2

[0294] Example 2: Selective cytotoxicity analysis of compounds in human lung cancer, breast cancer, colon cancer, acute leukemia cells and normal fibroblast models

[0295] Cells used in the experiment: human non-small cell lung cancer cells H460, paclitaxel-resistant human non-small cell lung cancer cells H460 TaxR; human breast cancer cell MCF-7 / ADR resistant to doxorubicin; human colon cancer cell HT29; human leukemia cell OP-1; human normal fibroblast NHFB.

[0296] Experimental method: sulforhodamine B (SRB) method (Vnicha Vichail & Kanyawim Kirtikara. Sulforhodamine B colorimetric assay for cytotoxicity screening. Nature Protocols 1, 2006, 1112-1116.)

[0297] Take H460 cells and H460 cells in the logarithmic growth phase TaxR cells, HT-29 cells, MCF-7 / ADR cells, OP-1 cells and NHFB cells, prepared into 3×10 4 ·mL -1 Add 100 μL of cell suspension to each well and inoculate in a 96-well plate in 5% CO 2 , cultured at 37°C for 24 hours, removed the supernatant, and add...

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Abstract

The invention relates to multi-substituted pyrido sulfur nitrogen 7-membered ring derivatives represented by a general formula I-1, wherein the derivatives have wide anti-tumor activities. In vitro cell test results show that the compounds provide good inhibition effects for multiple human tumor cell lines, wherein the human tumor cell lines comprise human leukemia cell line OP-1, human colon carcinoma cell line HT29, human lung cancer cell line H460, paclitaxel resistant human lung cancer cell line H460TaxR, adriamycin resistant human breast cancer cell line MCF-7 / Adr and the like. According to the present invention, pharmaceutical auxiliary materials can be mixed with the compounds of the present invention independently or mixtures of the compounds and effective components of other anti-tumor drugs to prepare pharmaceutical formulations for treatments of various tumor diseases. The compounds represented by the I-1 are prepared by carrying out condensation and oxidation on compounds represented by a formula I-2 and R7COZ (Z is OH or halogen).

Description

technical field [0001] The present invention relates to a class of low-molecular-weight compounds with a seven-membered pyridothiazane ring that can be used as anticancer drugs, their composition, and their preparation. The present invention also relates to methods for treating, alleviating and controlling tumor diseases, including administration of tumor cell growth inhibitors, alone or in combination with known therapies. The present invention also relates to the medicament prepared by using these compounds and the dosage thereof and their application in treating a series of diseases such as tumor diseases and cancers. These preparations can also be used concurrently with other treatments to achieve a therapeutic effect. Background technique [0002] Malignant tumors are currently one of the most serious diseases that endanger human health, and their fatality rate is second only to cardiovascular diseases. [0003] Lung cancer is currently the malignant tumor with the la...

Claims

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Application Information

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IPC IPC(8): C07D513/04A61K31/554A61P35/00
CPCC07D513/04A61P35/00
Inventor 柏旭闫兵项金宝张秋裴亚中
Owner CHANGCHUN DISCOVERY SCI
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